Top 10 Matches in WWE Monday Night Raw History

Written by Nick Miller

You don't always have to be watching a pay-per-view to catch some truly incredible match-ups. Welcome to and today, we're counting down the top 10 matches in Monday Night Raw history.
Top 10 Matches in Monday Night Raw History

You don’t always have to be watching a pay-per-view to catch some truly incredible match-ups. Welcome to and today, we’re counting down the top 10 matches in Monday Night Raw history.

We’ll be looking at the 10 most memorable and enjoyable matches that have ever taken place on Monday Night Raw. Let’s get started.

#10: The Rock vs. Mankind - February 15th, 1999

One of the defining feuds of the attitude era was the long-lasting rivalry between The Rock and Mick Foley. In this grueling ladder match for the then-WWF championship, Foley’s alter-ego Mankind faced off against the The Rock after months of back-and-forth and controversy over the championship. The already-injured Foley unsurprisingly took massive amounts of punishment from The Rock with brutal attacks by a chair and the ladder throughout the match. Just when it looked like Foley might be able to grab the title and retain his championship, interference by The Big Show gave The Rock the win, ensuring he would go on to face Stone Cold Steve Austin in the main event of Wrestlemania 15.

#9: Ric Flair vs. Edge - January 16, 2006

In an emotional and memorable bout, Intercontinental champion Ric Flair challenged Edge for his WWE championship in the first ever TLC match for the title in WWE history. During this battle of new school vs. old school, Edge brutalized the veteran Flair in front of his family watching from the front row (including future superstar Charlotte Flair). Both performers went all-out for the Raw main event, with Flair eventually being busted open and bleeding everywhere. After consistent interference by Lita, the 15-minute bout was won by Edge after knocking Flair off the top of the ladder and grabbing the title.

#8: Lita vs. Trish Stratus - December 6th, 2004

In the first-ever women’s championship main event on Raw, punk rock babyface Lita took on heel champion Trish Stratus for the Women’s Championship in a history-making match in Lita’s home state. Despite the bout’s relatively short length, the two women showed that they were both deserving of the main event slot with exciting standout moments and an intense back-and-forth that ended with the hometown hero Lita securing the pin on Stratus after a massive moonsault. Seeing two of the most important figures in modern women’s wrestling go all-out for the title in their first main event was exciting to say the least, and set the stage for the future of women’s wrestling in the company.

#7: The Shield vs. The Wyatt Family - March 3rd, 2014

In a huge crowd-pleasing main event, the company’s two red-hot stables met for a rematch of their Elimination Chamber bout weeks before.The Wyatt Family had defeated the Shield after tensions between the Hounds of Justice boiled over, leading to Dean Ambrose abandoning Seth Rollins and Roman Reigns mid-match. Memorable for both its in-ring performance work and storytelling, this high-octane Raw match culminated with Rollins bewing the one to abandon his team, leaving his partners outnumbered and giving Bray Wyatt, Luke Harper and Erick Rowan the win, hinting further towards the future dissolution of the Shield.

#6: Shawn Michaels vs. Shelton Benjamin - May 2nd, 2005

Perhaps the most surprising match on our list, this bout between Intercontinental Champion Shelton Benjamin and perennial fan-favorite Shawn Michaels took place in the first round of a tournament meant to decide a new number-one contender for the World Heavyweight Title. Benjamin held his own against the Heartbreak Kid, with the men delivering an utter classic including memorable moments such as a double kip-up and an explosive near-fall that made us believe Benjamin really could have beaten HBK. Though Michaels would lose in the second round, this early-round match was easily the stand-out of the tournament and helped legitimize Shelton Benjamin even further.

#5: Shawn Michaels vs. Triple H - December 29th, 2003

This all-out war between two best friends features everything you’d expect to find in a WWE match of this caliber. In the final Raw main event of 2003, Shawn Michaels challenged Triple H for the World Heavyweight Championship in an epic battle that lasted over 30 minutes. Featuring vicious attacks back-and-forth, Shawn Michaels appeared to eek out the win despite interference from Ric Flair until Raw GM and replacement referee Eric Bischoff ruled that both Michaels’ and Triple H’s shoulders were on the mat, leading to a draw. After this, Stone Cold Steve Austin returned from injury, hitting the ring to attack Bischoff for his questionable decision.

#4: Christian vs. Rob Van Dam - September 29th, 2003

The two men, both of whom have long histories with ladder matches, faced off in a Raw main event for the Intercontinental Championship held by Christian. Rob Van Dam was the clear fan-favorite in the bout, which went on for nearly 15 minutes of high-flying action and savage ladder offense. Both performers showed off their immense talent and in-ring chemistry together with inventive spots that led to an incredibly exciting 5-star Frog Splash from the top of the ladder by Van Dam, giving him enough time to climb the ladder and grab the title, becoming the new Intercontinental Champion.

#3: John Cena vs. CM Punk - February 25th, 2013

Cena and Punk had one of the hottest WWE rivalries of the past 10 years, and this Monday Night Raw classic was a perfect showcase of what the pair had to offer. After winning the 2013 Royal Rumble, Cena put his Wrestlemania main event slot on the line against Punk in a non-stipulation singles match. The bout lasted nearly 30 minutes, the pair playing on their history by each surviving the other’s most devastating moves. Cena would eventually land a second Attitude Adjustment on the straight-edge superstar, giving Cena his first major win over Punk.

#2: John Cena vs. Shawn Michaels - April 23rd, 2007

Two of the WWE’s all-time biggest stars faced off in this nearly hour-long master class on Raw only weeks after their Wrestlemania 23 main event. The two competed in the non-title match just 6 days before Cena would defend his WWE Championship against Michaels and 2 other men at Backlash, giving extra weight to the sheer endurance of both men in this bout. Michaels would eventually just barely come out on top after surviving an Attitude Adjustment and landing Sweet Chin Music on Cena, getting the cover with the last remaining energy he had left.

Honorable Mentions

Owen Hart vs. The British Bulldog - March 3rd, 1997

Bret Hart vs. The 1-2-3 Kid - July 11th, 1994

Seth Rollins vs. Neville - August 3rd, 2015

#1: CM Punk vs. Daniel Bryan - May 28th, 2012

Between their two highly-regarded matches at Over the Limit and Money in the Bank, these two fan-favorites had yet another face-off during CM Punk’s record-breaking world title reign. After losing at Over the Limit, Daniel Bryan had the opportunity to become number one contender once again for Punk’s championship by winning this match, which stacks up with either of the pair’s PPV bouts. Featuring an appearance by Bryan’s ex-girlfriend and Punk’s future-girlfriend AJ Lee, the pair pounded each other over the course of the 15-minute match until Bryan launched Punk into an exposed turnbuckle, giving him an arguably undeserved win. Most surprising part of this harrowing match? It wasn’t even the show’s main event…